Understanding Polymorphism in Organic Semiconductor Thin Films through Nanoconfinement

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Understanding crystal polymorphism is a long-standing challenge relevant to many fields, such as pharmaceuticals, organic semiconductors, pigments, food, and explosives. Controlling polymorphism of organic semiconductors (OSCs) in thin films is particularly important given that such films form the active layer in most organic electronics devices and that dramatic changes in the electronic properties can be induced even by small changes in the molecular packing. However, there are very few polymorphic OSCs for which the structure-property relationships have been elucidated so far. The major challenges lie in the transient nature of metastable forms and the preparation of phase-pure, highly crystalline thin films for resolving the crystal structures and evaluating the charge transport properties. Here we demonstrate that the nanoconfinement effect combined with the flow-enhanced crystal engineering technique is a powerful and likely material-agnostic method to identify existing polymorphs in OSC materials and to prepare the individual pure forms in thin films at ambient conditions. With this method we prepared high quality crystal polymorphs and resolved crystal structures of 6,13-bis(triisopropylsilylethynyl)pentacene (TIPS-pentacene), including a new polymorph discovered via in situ grazing incidence X-ray diffraction and confirmed by molecular mechanic simulations. We further correlated molecular packing with charge transport properties using quantum chemical calculations and charge carrier mobility measurements. In addition, we applied our methodology to a [1]benzothieno[3,2-b][1]1benzothiophene (BTBT) derivative and successfully stabilized its metastable form.
Publisher
AMER CHEMICAL SOC
Issue Date
2014-12
Language
English
Article Type
Article
Keywords

CHARGE-TRANSPORT; PHASE-TRANSITION; SINGLE-CRYSTALS; PENTACENE; GROWTH; TRANSFORMATIONS; PERFORMANCE; DENSITY; MODELS; TEMPERATURE

Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.136, no.49, pp.17046 - 17057

ISSN
0002-7863
DOI
10.1021/ja507179d
URI
http://hdl.handle.net/10203/207321
Appears in Collection
MS-Journal Papers(저널논문)
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